routines, Barry Winbolt's meetup, self-employed

Is working for yourself all it’s cracked up to be? Many people believe it is, but as a self-employed person from a long line of self-employed people I’d say “Maybe”.

Don’t get me wrong, I love working for myself and wouldn’t have it any other way. It works for me and always has done, but it is not a recipe for freedom that many people aspire to.

Unless you take precautions, leaving your job and becoming self-employed simply substitutes one set of problems (having to go to work, disliking your manager or boss, constant deadlines, mounting pressure, change upon change…) for others (paying the bills, generating business, overheads and running costs…).

But, for me, working for myself as a freelancer brings so many benefits that they easily outweigh the ‘real life’ aspects of paying bills (and taxes), being solely responsible for my success or failure, finding enough business, and all the rest.

I have had proper jobs, some good ones, and although I really enjoyed most of these stints in salary-land, ultimately I prefer being on my own with the freedom to do whatever I choose, and bear the consequences, good and bad.

It’s about mindset

Once you’ve understood that working for yourself means a totally new mindset and – at first at least working much harder – as long as you are the ‘self-employed type’ (see below), you’ll be on the road to success… maybe.

In the distant past I used to run workshops on making the move to self-employment, and more recently people have started to ask about this again, so I have been looking into it to see what’s available by way of guidance and advice. It’s been disappointing because, given that so many people aspire to creating a ‘lifestyle business’, there is precious little out there to help with the personal development aspects of making the shift.

What I’ve found in my research is that while there is plenty of information on the business aspects of working for yourself (banks, business plans, taxes and the rest), there is virtually nothing on the personal transformation needed for success. By ‘personal transformation’ I mean the psychological and emotional aspects of working for yourself, the practical considerations of managing your own time and the discipline and motivation needed when you work by yourself, particularly from home.

I am re-writing the workshop so sign up for my newsletter to find out when and how to join when I run online events. In the meantime, here are some considerations to check if self-employment would suit you.

  • Do you have an idea, concept or passion that you could build a business around?
  • Can you keep the ideas coming so that any failures can be replaced by new potential successes?
  • Can you get up and get on with your work, even on the days when you don’t want to?
  • Can you work on your own initiative, day after day, with no-one to guide you but yourself?
  • Are you prepared to commit to up to two years ‘learning the ropes’?
  • Can you survive on fluctuating income for a similar period?
  • Do you like your own company?
  • Do you have faith in your ideas, the confidence to apply them, and the initiative to ask for help when you get stuck?
  • Do you have the unstinting support of your spouse or partner?
  • Do you accept that failure, rejection and learning are as much a part of the process as earning, succeeding and recognition?

If you can answer “Yes” to half or more of these than I’d say go for it. Give yourself a time-limit and have a backup plan. Part of succeeding in self-employment is understanding when to abandon or change an idea that isn’t working, so it’s about flexibility and open-mindedness as much as it is about dogged persistence and determination.

I hope this gives you food for thought, and if it does, sign up here to keep up to date with my free training events.

I’m a psychologist, coach, and therapist. All my work is aimed at enabling people to improve personal aspects of their lives and work.